Hydrochloric Acid → HCID 70015285, compound

HRID 1370733Notes

Reaction equation

HRID 1370733 reaction equation
C([NH:4][C@H:5]([C:23]([O:25]C)=[O:24])[CH2:6][S:7]([C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)(=[O:9])=[O:8])(=O)C.Cl>C(O)(=O)C>[O:16]([C:13]1[CH:14]=[CH:15][C:10]([S:7]([CH2:6][C@@H:5]([C:23]([OH:25])=[O:24])[NH2:4])(=[O:9])=[O:8])=[CH:11][CH:12]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131723932HCID 131723932, compound

Product 1

HCID 70015285HCID 70015285, compoundYield 109.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of the titled compound of Example 9d (3.27 g, 8.66 mmol) in glacial acetic acid (18.5 mL) was heated until all solids dissolved and then concentrated HCl (18.5 mL) was added. The solution was heated at reflux for 4 hours. The mixture was concentrated to an off white solid. The solid was treated with toluene, concentrated, and triturated with diethyl ether afforded the title amino acid as a white solid (3.04 g, 98%). Elemental Anal. Calcd. for C15H16NO5SCl: C, 50.35; H, 4.51; N, 3.91; S, 8.96. Found: C, 50.21; H, 4.43; N, 3.92; S, 9.04.

Workup

  1. dissolutiondissolved
  2. temperatureThe solution was heated
  3. temperatureat reflux for 4 hours
  4. concentrationThe mixture was concentrated to an off white solid
  5. additionThe solid was treated with toluene
  6. concentrationconcentrated
  7. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-2a7388d8eae64bb1bf258ad752538503
Source dataset
uspto-grants-2003_06
Patent number
US06583299B1

Reaction notes

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